Organic electroluminescent device

ABSTRACT

There is provided an electroluminescent device including an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, the organic layer including at least a red light emitting layer, the organic layer containing a compound represented with the chemical formula C1, alone or in combination:  
                 
 
     wherein R 1  to R 4  each independently represents a hydrogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aralkyl group, wherein at least one of R 1  to R 4  is a di-aryl amino group represented with —NAr 1 Ar 2  where each of Ar 1  and Ar 2  independently indicates an aryl group having a carbon number of 6 to 20 both inclusive, wherein R 5  to R 12  each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, and wherein any two of R 1  to R 4  except diaryl amino group and R 5  to R 12  may form a ring.

BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention

[0002] The invention relates to an organic electroluminescent device,and more particularly to an organic electroluminescent device havingimproved light-emission characteristic.

[0003] 2. Description of the Related Art

[0004] An organic electroluminescent device (hereinafter, referred tosimply as “organic EL device”) is a light-emitting device under theprinciple that fluorescent material performs light emission byre-combination energy generated when holes introduced through an anodeand electrons introduced through a cathode are re-combined, whichre-combination is caused by applying an electric field to the organic ELdevice.

[0005] After the organic EL device driven at a low voltage and comprisedof a multi-layered structure has been reported by C. W. Tang and S. A.VanSlyke in Applied Physics Letters, Vol. 51, pp. 913, 1987, variousstudies have been made about an organic EL device composed of organicmaterial. The organic EL device suggested by C. W. Tang et al. includesa light-emitting layer composed of tris-(8-hydroxyquinolinol aluminum),and a hole-transporting layer composed of triphenyl di-amine. Themulti-layered structure provides advantages that holes can be injectedinto a light-emitting layer with a higher efficiency, that electronsinjected through a cathode can be blocked to thereby enhance ageneration efficiency of excitons generated by re-combination, and thatexcitons generated in a light-emitting layer can be shut in thelight-emitting layer.

[0006] An organic EL device generally has either a two-layered structureincluding a hole transporting layer and an electron transportinglight-emitting layer, or a three-layered structure including a holetransporting layer, a light-emitting layer, and an electron transportinglayer. Various attempts have been made about a device structure and amethod of fabrication in such a multi-layered structure device in orderto enhance an efficiency of re-combination of injected holes andelectrons.

[0007] As suggested in Japanese Unexamined Patent Publications Nos.8-20771, 8-40995, 8-40997, 8-259935, 8-543397, and 8-87122, triphenylamine derivative and aromatic diamine derivative of star-burst moleculessuch as 4, 4′4″-tris (3-methylphenylphenylamino) triphenylamine, andN,N′-diphenyl-N,N′-bis (3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine,are well known as materials of which a hole transporting layer iscomposed.

[0008] As materials of which an electron transporting layer is composed,oxadiazole derivative, triazole derivative and so on are well known.

[0009] As materials of which a light-emitting layer is composed, chelatecomplex such as (8-quiolinolate) aluminum complex, coumarin derivative,tetraphenylbutadiene derivative, bisstyrylarylene derivative, andoxadiazole derivative are well known. It has been also reported thatthose materials emit a light in a visible range including blue to redlights. For instance, those materials are used for color display device,as suggested in Japanese Unexamined Patent Publications 8-239655,7-138561, and 3-200289.

[0010] An organic EL device is free from a limitation that analternative current and a high voltage have to be applied thereto,unlike an inorganic EL device. In addition, it is considered that anorganic EL device could provide many colors due to variety in organiccompounds, and hence, an organic EL device is expected to apply to afull-color display.

[0011] In application of an organic EL device to a full-color display,it is necessary to have light-emission of three major colors, that is,red, green and blue. Many examples have been reported about greenlight-emission. For instance, there has been suggested a deviceincluding aluminum complex of 8-quinolinol Applied Physics Letters, Vol.51, pp. 913, 1987), and a device including diarylamine derivative(Japanese Unexamined Patent Publication No. 8-53397).

[0012] There have been reported many examples of blue light emittingdevices. For instance, Japanese Unexamined Patent Publications Nos.5-295359, 7-53955, and 6-132080 have suggested a device includingstilbene family compound, a device including triarylamine derivative,and a device including styrylized biphenyl compound, respectively.

[0013] Japanese Unexamined Patent Publication No. 8-245955 has suggestedan organic EL device in which various light-emitting materials emittingvarious colored lights may be selected by using an electron transportingmaterial having stability as a thin film, resulting in reduction inbrightness.

[0014] However, there are quite few examples about an organic EL deviceproviding red light emission. For instance, Japanese Unexamined PatentPublication 3-152897 has suggested a method of converting a wavelengthof a blue light in a fluorescent pigment layer. Japanese UnexaminedPatent Publications Nos. 7-272854, 7-288184, and 8-286033 have suggestedred light emission accomplished by doping red fluorescent pigment into agreen or blue light emitting layer. Examples of an organic EL deviceproviding red light emission are few relative to examples of an organicEL device providing green or blue emission.

[0015] Furthermore, the above-mentioned organic EL devices providing redlight emission cannot provide sufficient brightness, color purity,efficiency, and lifetime, and hence, need to be improved.

[0016] Apart from the Publications listed above, Japanese UnexaminedPatent Publication No. 3-791 has suggested an electric fieldlight-emitting device including a fluorescent light-emitting layercontaining perylene compound.

[0017] Japanese Unexamined Patent Publication No. 4-6795 has suggestedan organic electroluminescent device including an electrode throughwhich electrons are injected and which has at least two-layeredstructure.

[0018] Japanese Unexamined Patent Publication No. 4-334894 has suggestedan electric field light-emitting device including an organic thin film.The suggested electric field light-emitting device includes a layercomposed of a hole transporting light-emitting material, and a layercomposed of both a hole transporting light-emitting material and anelectron transporting material.

SUMMARY OF THE INVENTION

[0019] It is an object of the present invention to provide an organic ELdevice capable of providing a higher brightness than a brightness ofconventional ones.

[0020] Another object of the present invention is to provide an organicEL device capable of providing red light emission at a higher brightnessand in higher color purity than those of conventional ones.

[0021] The inventors have conducted experiments in order to solve theabove-mentioned problems, and it was found that an organic EL deviceincluding a light-emitting layer composed of perylene compound havingdiarylamino group at a particular position provides a higher brightnessthan a brightness of conventional organic EL devices.

[0022] It was also found that perylene compound had high holetransporting characteristic, and that both an organic EL deviceincluding a hole transporting layer composed of perylene compound, andan organic EL device including a thin film composed of perylene compoundand other hole transporting materials or electron transporting materialsprovide light-emission with a higher brightness than that ofconventional organic EL devices.

[0023] There is provided an electroluminescent device including (a) ananode, (b) a cathode, and (c) at least one organic layer sandwichedbetween the anode and the cathode, the organic layer including at leasta light-emitting layer, the organic layer containing a compoundrepresented with the chemical formula C1, alone or in combination:

[0024] wherein R¹ to R⁴ each independently represents a hydrogen atom, ahydroxyl group, a substituted or unsubstituted amino group, a nitrogroup, a substituted or unsubstituted alkyl group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted cycloalkylgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted aromatic hydrocarbon group, a substituted or unsubstitutedaromatic heterocyclic group, or a substituted or unsubstituted aralkylgroup,

[0025] wherein at least one of R¹ to R⁴ is a di-aryl amino grouprepresented with —NAr¹Ar² where each of Ar¹ and Ar² independentlyindicates an aryl group having a carbon number of 6 to 20 bothinclusive,

[0026] wherein R⁵ to R¹² each independently represents a hydrogen atom,a halogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, or asubstituted or unsubstituted aralkyl group, a substituted orunsubstituted aryloxy group, a substituted or unsubstitutedalkoxycarbonyl group, or a carboxyl group, and

[0027] wherein any two of R¹ to R⁴ except diaryl amino group and R⁵ toR¹² may form a ring.

[0028] It is preferable that each of the Ar¹ and Ar² includes asubstituent.

[0029] It is preferable that the organic layer includes a holetransporting layer containing the compound represented with the chemicalformula C1, alone or in combination.

[0030] The inventors have conducted experiments in order to solve theabove-mentioned problems, and it was found that an organic EL deviceincluding a light-emitting layer composed of bisanthrene compoundprovides a higher brightness than a brightness of conventional organicEL devices.

[0031] It was also found that bisanthrene compound had high holetransporting characteristic, and that both an organic EL deviceincluding a hole transporting layer composed of bisanthrene compound,and an organic EL device including a thin film composed of bisanthrenecompound and other hole transporting materials or electron transportingmaterials provide light-emission with a higher brightness than that ofconventional organic EL devices.

[0032] There is further provided an electroluminescent device including(a) an anode, (b) a cathode, and (c) at least one organic layersandwiched between the anode and the cathode, the organic layerincluding at least a light-emitting layer, the organic layer containinga bisanthrene compound represented with the chemical formula C2, aloneor in combination:

[0033] wherein R¹ to R¹⁴ each independently represents a hydrogen atom,a halogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group, and

[0034] wherein any two of R¹ to R¹⁴ may form a ring.

[0035] It is preferable that the organic layer includes a hole orelectron transporting layer containing the compound represented with thechemical formula C2, alone or in combination. It is also preferable thatthe organic layer includes both a hole transporting layer and anelectron transporting layer, the electron transporting layer containingthe compound represented with the chemical formula C2, alone or incombination.

[0036] It was also found that an organic EL device including alight-emitting layer composed of a particular benzoperylene compoundemit a light at a higher brightness than a brightness of conventionalorganic EL devices.

[0037] It was also found that the above-mentioned benzoperylene compoundhad high carrier transporting characteristic, and that both an organicEL device including a hole or electron transporting layer composed ofthe benzoperylene compound, and an organic EL device including a thinfilm composed of the benzoperylene compound and other hole transportingmaterials or electron transporting materials provide light-emission witha higher brightness than that of conventional organic EL devices.

[0038] It was also found that an organic EL device including inparticular a diarylamino group as a substituent among benzoperylenecompounds provides light-emission with a higher brightness.

[0039] It was further found that an organic EL device including inparticular an aryl group having a styryl group as a substituent, amongbenzoperylene compounds having a diarylamino group as a substituentprovides light-emission with a higher brightness.

[0040] There is still further provided an electroluminescent deviceincluding (a) an anode, (b) a cathode, and (c) at least one organiclayer sandwiched between the anode and the cathode, the organic layerincluding at least a light-emitting layer, the organic layer containinga benzoperylene compound represented with the chemical formula C3, aloneor in combination:

[0041] wherein R¹ to R¹⁴ each independently represents a hydrogen atom,a halogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group, and

[0042] wherein any two of R¹ to R¹⁴ may form a ring.

[0043] It is preferable that the organic layer includes a hole orelectron transporting layer containing the benzoperylene compoundrepresented with the chemical formula C3, alone or in combination.

[0044] It is preferable that at least one of R¹ to R¹⁴ is a di-arylamino group represented with —NAr¹Ar² where each of Ar¹ and Ar²independently indicates an aryl group having a carbon number of 6 to 20both inclusive, in which case, the aryl group may have a substituent. Itis also preferable that at least one of R¹ to R¹⁴ is a di-aryl aminogroup represented with —NAr¹Ar² where each of Ar¹ and Ar² independentlyindicates an aryl group having a carbon number of 6 to 20 bothinclusive, and at least one of the Ar¹ and Ar² includes a substituted orunsubstituted styryl group as a substituent, in which case, the arylgroup may have a substituent.

[0045] It was also found that an organic EL device including alight-emitting layer composed of a particular terylene compound emit alight at a higher brightness than a brightness of conventional organicEL devices.

[0046] It was also found that the above-mentioned terylene compound hadhigh carrier transporting characteristic, and that both an organic ELdevice including a hole or electron transporting layer composed of theterylene compound, and an organic EL device including a thin filmcomposed of the terylene compound and other hole transporting materialsor electron transporting materials provide light-emission with a higherbrightness than that of conventional organic EL devices.

[0047] It was also found that an organic EL device including inparticular a diarylamino group as a substituent among terylene compoundsprovides light-emission with a higher brightness.

[0048] It was further found that an organic EL device including inparticular an aryl group having a styryl group as a substituent, amongterylene compounds having a diarylamino group as a substituent provideslight-emission with a higher brightness.

[0049] There is yet further provided an electroluminescent deviceincluding (a) an anode, (b) a cathode, and (c) at least one organiclayer sandwiched between the anode and the cathode, the organic layerincluding at least a light-emitting layer, the organic layer containinga terylene compound represented with the chemical formula C4, alone orin combination:

[0050] wherein R¹ to R¹⁶ each independently represents a hydrogen atom,a halogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group, and

[0051] wherein any two of R¹ to R¹⁶ may form a ring.

[0052] It is preferable that the organic layer includes a hole orelectron transporting layer containing the terylene compound representedwith the chemical formula C4, alone or in combination.

[0053] It is preferable that at least one of R¹ to R¹⁴ is a di-arylamino group represented with —NAr¹Ar² where each of Ar¹ and Ar²independently indicates an aryl group having a carbon number of 6 to 20both inclusive, in which case, the aryl group may have a substituent.

[0054] It is preferable that at least one of R¹ to R¹⁴ is a di-arylamino group represented with —NAr¹Ar² where each of Ar¹ and Ar²independently indicates an aryl group having a carbon number of 6 to 20both inclusive, and at least one of the Ar¹ and Ar² includes asubstituted or unsubstituted styryl group as a substituent, in whichcase, the aryl group may have a substituent.

[0055] It is preferable that the anode has a work function equal to orgreater than 4.5 eV, in which case, it is preferable that the cathodehas a smaller work function than that of the anode.

[0056] It is preferable that the organic layer has a thickness in therange of 1 nanometer to 1 micrometer both inclusive.

[0057] The firstly mentioned organic EL device includes a compoundhaving a chemical constitution represented with the chemical formula C1.In the chemical formula C1, R¹ to R⁴ each independently represents ahydrogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a substituted or unsubstituted alkyl group, asubstituted or unsubstituted alkenyl group, a substituted orunsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, or asubstituted or unsubstituted aralkyl group. At least one of R¹ to R⁴ isa di-aryl amino group represented with —NAr¹Ar² where each of Ar¹ andAr² independently indicates an aryl group having a carbon number of 6 to20 both inclusive. In the chemical formula C1, R⁵ to R¹² eachindependently represents a hydrogen atom, a halogen atom, a hydroxylgroup, a substituted or unsubstituted amino group, a nitro group, acyano group, a substituted or unsubstituted alkyl group, a substitutedor unsubstituted alkenyl group, a substituted or unsubstitutedcycloalkyl group, a substituted or unsubstituted alkoxy group, asubstituted or unsubstituted aromatic hydrocarbon group, a substitutedor unsubstituted aromatic heterocyclic group, or a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group.

[0058] The secondly mentioned organic EL device includes a compoundhaving a chemical constitution represented with the chemical formula C2.In the chemical formula C2, R¹ to R¹⁴ each independently represents ahydrogen atom, a halogen atom, a hydroxyl group, a substituted orunsubstituted amino group, a nitro group, a cyano group, a substitutedor unsubstituted alkyl group, a substituted or unsubstituted alkenylgroup, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aromatichydrocarbon group, a substituted or unsubstituted aromatic heterocyclicgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryloxy group, a substituted or unsubstitutedalkoxycarbonyl group, or a carboxyl group.

[0059] The thirdly mentioned organic EL device includes a compoundhaving a chemical constitution represented with the chemical formula C3.In the chemical formula C3, R¹ to R¹⁴ each independently represents ahydrogen atom, a halogen atom, a hydroxyl group, a substituted orunsubstituted amino group, a nitro group, a cyano group, a substitutedor unsubstituted alkyl group, a substituted or unsubstituted alkenylgroup, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aromatichydrocarbon group, a substituted or unsubstituted aromatic heterocyclicgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryloxy group, a substituted or unsubstitutedalkoxycarbonyl group, or a carboxyl group.

[0060] The fourthly mentioned organic EL device includes a compoundhaving a chemical constitution represented with the chemical formula C4.In the chemical formula C4, R¹ to R¹⁸ each independently represents ahydrogen atom, a halogen atom, a hydroxyl group, a substituted orunsubstituted amino group, a nitro group, a cyano group, a substitutedor unsubstituted alkyl group, a substituted or unsubstituted alkenylgroup, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aromatichydrocarbon group, a substituted or unsubstituted aromatic heterocyclicgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryloxy group, a substituted or unsubstitutedalkoxycarbonyl group, or a carboxyl group.

[0061] The halogen atom includes fluorine, chlorine, bromine, andiodine.

[0062] The substituted or unsubstituted amino group is represented by—NX¹X² wherein X¹ and X² each independently represent a hydrogen atom, amethyl group, an ethyl group, a propyl group, an isopropyl group, ann-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, ann-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-triburomopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, a 1,2,3-trinitropropyl group, a phenyl group,a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthrylgroup, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group,a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a4-styrylphenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terpheny-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group, a 2-pyrrolyl group, a 3-pyrrolylgroup, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a4-pyridinyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolylgroup, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a1-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a2-furyl group, a 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranylgroup, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranylgroup, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a3-benzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranylgroup, a 6-isobenzofuranyl group, a 7-isobenzofuranyl group, a2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolylgroup, a 6-quinolyl group, a 7-quinolyl group, a 8-quinolyl group, a1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, a8-isoquinolyl group, a 2-quinoxalyl group, a 5-quinoxalyl group, a6-quinoxalyl group, a 1-carbazolyl group, a 2-carbazolyl group, a3-carbazolyl group, a 4-carbazolyl group, a 1-phenanthridinyl group, a2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinylgroup, a 6-phenanthridinyl group, a 7-phenanthridinyl group, a8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinylgroup, a 1-acrydinyl group, a 2-acrydinyl group, a 3-acrydinyl group, a4-acrydinyl group, a 9-acrydinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxazinylgroup, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl-1-indolyl group, a4-t-butyl-1-indolyl group, a 2-t-butyl-3-indolyl group, a4-t-butyl-3-indolyl group, or the like.

[0063] The substituted or unsubstituted alkyl group includes, forexample, a methyl group, an ethyl group, a propyl group, an isopropylgroup, an n-butyl group, an s-butyl group, an isobutyl group, a t-butylgroup, an n-pentyl group, an n-hexyl group, an n-heptyl group, ann-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

[0064] The substituted or unsubstituted alkenyl group includes, forexample, a vinyl group, an allyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylvinyl group,a styryl group, a 2,2-diphenylvinyl group, a 1,2-diphenylvinyl group, a1-methylally group, a 1,1-dimethylallyl group, a 2-methylally group, a1-phenylally group, a 2-phenylallyl group, a 3-phenylally group, a3,3-diphenylally group, a 1,2-dimethylally group, a 1-phenyl-1-butenylgroup, and a 3-phenyl-1-butenyl group.

[0065] The substituted or unsubstituted cycloalkyl group includes, forexample, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, acyclohexyl group, and a 4-methylcyclohexyl group.

[0066] The substituted or unsubstituted alkoxy group is a grouprepresented by —OY wherein Y represents, for example, a methyl group, anethyl group, a propyl group, an isopropyl group, an n-butyl group, ans-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, ann-hexyl group, an n-heptyl group, an n-octyl group, a hydroxymethylgroup, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

[0067] The substituted or unsubstituted aromatic hydrocarbon groupincludes, for example, a phenyl group, a 1-naphthyl group, a 2-naphthylgroup, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a 3-biphenylylgroup, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terpheny-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, and a 4″-t-butyl-p-terphenyl-4-yl group.

[0068] Further, the substituted or unsubstituted aromatic heterocyclicgroup includes, for example, a 1-pyrrolyl group, a 2-pyrrolyl group, a3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinylgroup, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolyl group, a3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-benzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolylgroup, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a7-quinolyl group, a 8-quinolyl group, a 1-isoquinolyl group, a3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a6-isoquinolyl group, a 7-isoquinolyl group, a 8-isoquinolyl group, a2-quinoxalyl group, a 5-quinoxalyl group, a 6-quinoxalyl group, a1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a4-carbazolyl group, a 9-carbazolyl group, a 1-phenanthridinyl group, a2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinylgroup, a 6-phenanthridinyl group, a 7-phenanthridinyl group, a8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinylgroup, a 1-acrydinyl group, a 2-acrydinyl group, a 3-acrydinyl group, a4-acrydinyl group, a 9-acrydinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl-1-indolyl group, a 4-t-butyl-1-indolyl group, a2-t-butyl-3-indolyl group, and a 4-t-butyl-3-indolyl group.

[0069] The substituted or unsubstituted aralkyl group includes, forexample, a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a2-phenylisopropyl group, a phenyl-t-butyl group, an a-naphthylmethylgroup, a 1-a-naphthylethyl group, a 2-a-naphthylethyl group, a1-a-naphthylisopropyl group, a 2-a-naphthylisopropyl group, ab-naphthylmethyl group, a 1-b-naphthylethyl group, a 2-b-naphthylethylgroup, a 1-b-naphthylisopropyl group, a 2-b-naphthylisopropyl group, a1-pyrrolylmethyl group, a 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group.

[0070] The substituted or unsubstituted aryloxy group is represented by—OZ wherein Z represents a phenyl group, a 1-naphthyl group, a2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthrylgroup, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthrylgroup, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenylgroup, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenylgroup, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terpheny-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, a 4″-t-butyl-p-terphenyl-4-yl group, a2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinylgroup, a 3-pyridinyl group, a 4-pyridinyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolyl group, a4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a ³-benzofuranyl group, a 4-isobenzofuranylgroup, a 5-sobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group,a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a7-isoquinolyl group, a 8-isoquinolyl group, a 2-quinoxalyl group, a5-quinoxalyl group, a 6-quinoxalyl group, a 1-carbazolyl group, a2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinylgroup, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a7-phenanthridinyl group, a 8-phenanthridinyl group, a 9-phenanthridinylgroup, a 10-phenanthridinyl group, a 1-acrydinyl group, a 2-acrydinylgroup, a 3-acrydinyl group, a 4-acrydinyl group, a 9-acrydinyl group, a1,7-phenanthrolin-2-yl group, a 1,7-phenanthrolin-3-yl group, a1,7-phenanthrolin-4-yl group, a 1,7-phenanthrolin-5-yl group, a1,7-phenanthrolin-6-yl group, a 1,7-phenanthrolin-8-yl group, a1,7-phenanthrolin-9-yl group, a 1,7-phenanthrolin-10-yl group, a1,8-phenanthrolin-2-yl group, a 1,8-phenanthrolin-3-yl group, a1,8-phenanthrolin-4-yl group, a 1,8-phenanthrolin-5-yl group, a1,8-phenanthrolin-6-yl group, a 1,8-phenanthrolin-7-yl group, a1,8-phenanthrolin-9-yl group, a 1,8-phenanthrolin-10-yl group, a1,9-phenanthrolin-2-yl group, a 1,9-phenanthrolin-3-yl group, a1,9-phenanthrolin-4-yl group, a 1,9-phenanthrolin-5-yl group, a1,9-phenanthrolin-6-yl group, a 1,9-phenanthrolin-7-yl group, a1,9-phenanthrolin-8-yl group, a 1,9-phenanthrolin-10-yl group, a1,10-phenanthrolin-2-yl group, a 1,10-phenanthrolin-3-yl group, a1,10-phenanthrolin-4-yl group, a 1,10-phenanthrolin-5-yl group, a2,9-phenanthrolin-1-yl group, a 2,9-phenanthrolin-3-yl group, a2,9-phenanthrolin-4-yl group, a 2,9-phenanthrolin-5-yl group, a2,9-phenanthrolin-6-yl group, a 2,9-phenanthrolin-7-yl group, a2,9-phenanthrolin-8-yl group, a 2,9-phenanthrolin-10-yl group, a2,8-phenanthrolin-1-yl group, a 2,8-phenanthrolin-3-yl group, a2,8-phenanthrolin-4-yl group, a 2,8-phenanthrolin-5-yl group, a2,8-phenanthrolin-6-yl group, a 2,8-phenanthrolin-7-yl group, a2,8-phenanthrolin-9-yl group, a 2,8-phenanthrolin-10-yl group, a2,7-phenanthrolin-1-yl group, a 2,7-phenanthrolin-3-yl group, a2,7-phenanthrolin-4-yl group, a 2,7-phenanthrolin-5-yl group, a2,7-phenanthrolin-6-yl group, a 2,7-phenanthrolin-8-yl group, a2,7-phenanthrolin-9-yl group, a 2,7-phenanthrolin-10-yl group, a1-phenazinyl group, a 2-phenazinyl group, a 1-phenothiazinyl group, a2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl-1-indolyl group, a 4-t-butyl-1-indolyl group, a2-t-butyl-3-indolyl group, a 4-t-butyl-3-indolyl group, or the like.

[0071] The substituted or unsubstituted alkoxycarbonyl group isrepresented by —COOY wherein Y represents a methyl group, an ethylgroup, a propyl group, an isopropyl group, an n-butyl group, an s-butylgroup, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexylgroup, an n-heptyl group, an n-octyl group, a hydroxymethyl group, a1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxyisobutyl group,a 1,2-dihydroxyethyl group, a 1,3-dihydroxyisopropyl group, a2,3-dihydroxy-t-butyl group, a 1,2,3-trihydroxypropyl group, achloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a2-chloroisobutyl group, a 1,2-dichloroethyl group, a1,3-dichloroisopropyl group, a 2,3-dichloro-t-butyl group, a1,2,3-trichloropropyl group, a bromomethyl group, a 1-bromoethyl group,a 2-bromoethyl group, a 2-bromoisobutyl group, a 1,2-dibromoethyl group,a 1,3-dibromoisopropyl group, a 2,3-dibromo-t-butyl group, a1,2,3-triburomopropyl group, an iodomethyl group, a 1-iodoethyl group, a2-iodoethyl group, a 2-iodoisobutyl group, a 1,2-diiodoethyl group, a1,3-diiodoisopropyl group, a 2,3-diiodo-t-butyl group, a1,2,3-triiodopropyl group, an aminomethyl group, a 1-aminoethyl group, a2-aminoethyl group, a 2-aminoisobutyl group, a 1,2-diaminoethyl group, a1,3-diaminoisopropyl group, a 2,3-diamino-t-butyl group, a1,2,3-triaminopropyl group, a cyanomethyl group, a 1-cyanoethyl group, a2-cyanoethyl group, a 2-cyanoisobutyl group, a 1,2-dicyanoethyl group, a1,3-dicyanoisopropyl group, a 2,3-dicyano-t-butyl group, a1,2,3-tricyanopropyl group, a nitromethyl group, a 1-nitroethyl group, a2-nitroethyl group, a 2-nitroisobutyl group, a 1,2-dinitroethyl group, a1,3-dinitroisopropyl group, a 2,3-dinitro-t-butyl group, a1,2,3-trinitropropyl group, or the like.

[0072] Further, the bivalent group that forms a ring includes, forinstance, a tetramethylene group, a pentamethylene group, ahexamethylene group, a diphenylmethan-2,2-diyl group, adiphenylethan-3,3′-diyl group, and a diphenylpropan-4,4′-diyl group.

[0073] An aryl group having the carbon number in the range of 6 to 20both inclusive includes, for instance, a phenyl group, a naphthyl group,an antoryl group, a phenanthryl group, a naphthasenyl group, and apyrenyl group.

[0074] A substituent of an aryl group includes, for instance, a halogenatom, a hydroxyl group, a substituted or unsubstituted amino group, anitro group, a cyano group, a substituted or unsubstituted alkyl group,a substituted or unsubstituted alkenyl group, a substituted orunsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group.

[0075] A styryl group as a substituent of Ar¹ and Ar² includes, forinstance, an unsubstituted styryl group, 2,2-diphenylvinyl group. Asubstituent of the terminal phenyl group includes, for instance, asubstituted styryl group and a substituted 2,2-diphenyvinyl groupincluding a halogen atom, a hydroxyl group, a substituted orunsubstituted amino group, a nitro group, a cyano group, a substitutedor unsubstituted alkyl group, a substituted or unsubstituted alkenylgroup, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aromatichydrocarbon group, a substituted or unsubstituted aromatic heterocyclicgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryloxy group, a substituted or unsubstitutedalkoxycarbonyl group, or a carboxyl group.

[0076] Hereinbelow are shown examples of a compound represented with theabove-mentioned chemical formula C1 constituting an organic EL device inaccordance with the present invention. However, it should be noted thata compound represented with the chemical formula C1 is not to be limitedto the examples shown hereinbelow.

[0077] Hereinbelow are shown examples of a compound represented with theabove-mentioned chemical formula C2 constituting an organic EL device inaccordance with the present invention. However, it should be noted thata compound represented with the chemical formula C2 is not to be limitedto the examples shown hereinbelow.

[0078] Hereinbelow are shown examples of a benzoperylene compoundrepresented with the above-mentioned chemical formula C3 constituting anorganic EL device in accordance with the present invention. However, itshould be noted that a benzoperylene compound represented with thechemical formula C3 is not to be limited to the examples)shownhereinbelow.

[0079] Hereinbelow are shown examples of a compound represented with theabove-mentioned chemical formula C4 constituting an organic EL device inaccordance with the present invention. However, it should be noted thata compound represented with the chemical formula C4 is not to be limitedto the examples shown hereinbelow.

[0080] An organic EL device in accordance with the present inventionincludes an anode, a cathode, and one or more organic thin layer(s)sandwiched between the anode and the cathode. Specifically, the organicEL device may be comprised of:

[0081] (A) an anode 2, a light-emitting layer 4, and a cathode 6 asillustrated in FIG. 1;

[0082] (B) an anode 2, a hole transporting layer 3, a light-emittinglayer 4, an electron transporting layer 5, and a cathode 6 asillustrated in FIG. 2;

[0083] (C) an anode 2, a light-emitting layer 4, an electrontransporting layer 5, and a cathode 6 as illustrated in FIG. 3; or

[0084] (D) an anode 2, a hole transporting layer 3, a light-emittinglayer 4, and a cathode 6 as illustrated in FIG. 4.

[0085] The chemical compounds represented with C1, C2, C3 and C4 may becontained in any one of the above-mentioned light-emitting layer, holetransporting layer, and electron transporting layer. As an alternative,the chemical compounds represented with C1, C2, C3 and C4 may be dopedinto other hole transporting materials, light-emitting materials, orelectron transporting materials.

[0086] A material of which a hole transporting layer constituting anorganic EL device in accordance with the present invention is composedis not limited to a particular one. Any compound may be used, if it isusually used as a hole transporting material.

[0087] For instance, the compounds represented with the followingchemical formulas [1] to [6] may be employed as a material of which ahole transporting layer is composed: triphenyl diamine such as bis(di(p-tlyl) aminophenyl)-1,1′-cyclohexane [01], N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02], andN,N′-diphenyl-N-N-bis (1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03]; andstar-burst type molecules [04] to [06].

[0088] A material of which an electron transporting layer constitutingan organic EL device in accordance with the present invention iscomposed is not limited to a particular one. Any compound may be used,if it is usually used as an electron transporting material.

[0089] For instance, the compounds represented with the followingchemical formulas [7] to [14] may be employed as a material of which anelectron transporting layer is composed: an oxadiazole derivative suchas 2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole [07] andbis{2-(4-t-butylphenyl)-1,3,4-oxadiazole}-m-phenylene [08]; a triazolederivative [09] or [10]; or quinolinol family metal complexes [11] to[14].

[0090] An anode of an organic thin film EL device injects holes into ahole transporting layer, and hence, it is preferable that a holetransporting layer has a work function equal to or greater than 4.5 eV.For example, an anode of an organic EL device in accordance with thepresent invention is composed of indium oxide-tin alloy (ITO), tin oxide(NESA), gold, silver, platinum, or copper.

[0091] A cathode of an organic EL device injects electrons into anelectron transporting layer and a light-emitting layer, and hence, it ispreferable that a cathode has a smaller work function than that of ananode. A material of which a cathode is composed in an organic EL devicein accordance with the present invention is not limited to a particularone. For instance, a material of which a cathode is composed includesindium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminumalloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, andmagnesium-silver alloy.

[0092] Layers constituting an organic EL device in accordance with thepresent invention may be formed by any processes. For instance, aprocess such as conventional vacuum evaporation and spin coating may beemployed. A thin organic layer including a compound represented with theabove-mentioned chemical formulas C1, C2, C3 or C4 may be formed byconventional vacuum evaporation, molecular beam epitaxy (MBE), dippinginto a solution in which a solvent is dissolved, spin coating, casting,bar coating, or roll coating.

[0093] A thickness of organic layers constituting an organic EL devicein accordance with the present invention is not limited to a particularone. In general, a too small thickness of an organic layer would cause adefect such as pin-hole. On the contrary, a too great thickness of anorganic layer would require a high voltage to be applied to an organicEL device, which would cause a problem of reduction in efficiency.Hence, it is preferable that each of organic layers in an organic ELdevice in accordance with the present invention has a thickness in therange of 1 nm to 1 μm both inclusive.

[0094] The above and other objects and advantageous features of thepresent invention will be made apparent from the following descriptionmade with reference to the accompanying drawings, in which likereference characters designate the same or similar parts throughout thedrawings.

BRIEF DESCRIPTION OF THE DRAWINGS

[0095]FIG. 1 is a cross-sectional view of an organic EL device inaccordance with an embodiment of the present invention.

[0096]FIG. 2 is a cross-sectional view of an organic EL device inaccordance with another embodiment of the present invention.

[0097]FIG. 3 is a cross-sectional view of an organic EL device inaccordance with still another embodiment of the present invention.

[0098]FIG. 4 is a cross-sectional view of an organic EL device inaccordance with yet another embodiment of the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0099] Hereinbelow are explained embodiments of an organic EL deviceincluding an organic layer containing a compound represented with thechemical formula C1.

[Synthesis Example 1] Synthesis of Compound X1 (3-diphenylaminoperylene)

[0100] The following compounds were introduced into a vessel: (a)3-bromoperylene; (b) diphenylamine; (c) potassium carbonate; (d) copperpower; and (e) nitrobenzene. Then, the mixture was stirred at 200degrees centigrade for 40 hours. After reaction has finished,nitrobenzene was removed under a reduced pressure. Then, chlorofom wasadded to the mixture, and filtered for removing inorganic materials. Afiltrate was condensed, and then, impurities were removed by silica gelcolumn chromatography employing ligroin. As a result, there was obtaineda target material, 3-diphenylaminoperylene.

[Synthesis Example 2] Synthesis of Compound X2 (3,10-bisdiphenylaminoperylene)

[0101] The same process as the process carried out in Synthesis Example1 was carried out except that 3,10-dibromoperylene was used in place of3-bromoperylene. Thus, there was obtained a target material,3,10-bisdiphenylaminoperylene.

[Synthesis Example 3] Synthesis of Compound X3 (3,9-bis(di-p-tolylamino)perylene)

[0102] The same process as the process carried out in Synthesis Example1 was carried out except that 3,9-dichloroperylene was used in place of3-bromoperylene, and that di-p-tolylamine was used in place ofdiphenylamine. Thus, there was obtained a target material,3,9-bis(di-p-tolylamino) perylene.

[0103] In the later mentioned embodiments 1 to 3, a red light emittinglayer includes the compound represented with the chemical formula C1. Inthe embodiments 4 to 7, a red light emitting layer includes a thin filmcomposed of both the compound represented with the chemical formula C1and a hole transporting material. In the embodiments 8 to 10, a redlight emitting layer includes a thin film composed of both the compoundrepresented with the chemical formula C1 and an electron transportingmaterial. In the embodiments 11 to 13, a hole transporting layerincludes the compound represented with the chemical formula C1.

[Embodiment 1]

[0104] An organic EL device in accordance with the embodiment 1 has across-section as illustrated in FIG. 1. That is, the organic EL devicein accordance with the embodiment 1 is comprised of a glass substrate 1,an anode 2 and a cathode 6 formed on the glass substrate 1, and a redlight emitting layer 4 sandwiched between the anode 2 and the cathode 6.

[0105] The organic EL device in accordance with the embodiment 1 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, the red light emitting layer 4 composed of theabove-mentioned compound X1 was formed on the anode 2 by a thickness of40 nm by vacuum evaporation. Then, a magnesium-silver alloy film wasformed as the cathode 6 on the red light emitting layer 4 by a thicknessof 200 nm by vacuum evaporation. Thus, there was completed the organicEL device in accordance with the embodiment 1.

[0106] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 100 cd/m².

[Embodiment 2]

[0107] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound X2, to thereby fabricate an organic ELdevice in accordance with embodiment 2.

[0108] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 200 cd/m².

[Embodiment 3]

[0109] An organic EL device in -accordance with the embodiment 3 has thesame cross-section as that of the organic EL device in accordance withthe embodiment 1, illustrated in FIG. 1. Hereinbelow is explained stepsof fabricating an organic EL device in accordance with the embodiment 3.

[0110] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film acted as the anode 2. Then, the redlight emitting layer 4 was formed on the anode 2 by a thickness of 40 nmby spin coating in which chloroform solution containing theabove-mentioned compound X3 dissolved therein was used. Then, amagnesium-silver alloy film was formed as the cathode 6 on the red lightemitting layer 4 by a thickness of 200 nm by vacuum evaporation. Thus,there was completed the organic EL device in accordance with theembodiment 3.

[0111] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 180 cd/m².

[Embodiment 4]

[0112]FIG. 2 illustrates a cross-section of an organic EL device inaccordance with the embodiment 4. The organic EL device in accordancewith the embodiment 4 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3, a red light emitting layer 4, and an electrontransporting layer 5 all sandwiched between the anode 2 and the cathode6.

[0113] The organic EL device in accordance with the embodiment 4 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a film composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, the red light emitting layer 4 composed of theabove-mentioned compound X1 was formed on the hole transporting layer 3by a thickness of 40 nm by vacuum evaporation. Then, a film composed of2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole [07] was formed asthe electron transporting layer 5 on the red light emitting layer 4 by athickness of 20 nm by vacuum evaporation. Then, a film composed ofmagnesium-silver alloy was formed as the cathode 6 on the electrontransporting layer 5 by a thickness of 200 nm by vacuum evaporation.Thus, there was completed the organic EL device in accordance with theembodiment 4.

[0114] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 970 cd/m².

[Embodiment 5]

[0115] The same steps as the steps carried out in the above-mentionedembodiment 4 were carried out except that the red light emitting layer 4was composed of the compound X2, to thereby fabricate an organic ELdevice in accordance with embodiment 5.

[0116] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1050 cd/m².

[Embodiment 6]

[0117] The same steps as the steps carried out in the above-mentionedembodiment 4 were carried out except that the red light emitting layer 4was composed of the compound X3, that the hole transporting layer 3 wascomposed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03], and that the electrontransporting layer 5 was composed ofbis{2-(4-t-butylphenyl)-1,3,4-oxadiazole}-m-phenylene [08], to therebyfabricate an organic EL device in accordance with embodiment 6.

[0118] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1400 cd/m².

[Embodiment 7]

[0119] The same steps as the steps carried out in the above-mentionedembodiment 4 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [04], thatthe red light emitting layer 4 was composed of the compound X3, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [11], to thereby fabricate an organic ELdevice in accordance with embodiment 6.

[0120] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2000 cd/m².

[Embodiment 8]

[0121]FIG. 3 illustrates a cross-section of an organic EL device inaccordance with the embodiment 8. The organic EL device in accordancewith the embodiment 8 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a red lightemitting layer 4 and an electron transporting layer 5 both sandwichedbetween the anode 2 and the cathode 6.

[0122] The organic EL device in accordance with the embodiment 8 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a thin film was formed as the red light emittinglayer 4 on the anode 2 by a thickness of 50 nm by co-evaporation. Thisthin film was composed of both N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] and the above-mentionedcompound X2 at a weight ratio of 1:10. Then, a film composed of triazolederivative [09] was formed as the electron transporting layer 5 on thered light emitting layer 4 by a thickness of 50 nm by vacuumevaporation. Then, a magnesium-silver alloy film was formed as thecathode 6 on the electron transporting layer 5 by a thickness of 200 nmby vacuum evaporation. Thus, there was completed the organic EL devicein accordance with the embodiment 8.

[0123] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1030 cd/m².

[Embodiment 9]

[0124] The same steps as the steps carried out in the above-mentionedembodiment 8 were carried out except that the above-mentioned compoundX3 was used in place of the compound X2, to thereby fabricate an organicEL device in accordance with embodiment 9.

[0125] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1620 cd/m².

[Embodiment 10]

[0126] An organic EL device in accordance with the embodiment 10 has thesame cross-section as that of the organic EL device in accordance withthe embodiment 8, illustrated in FIG. 3. Hereinbelow is explained stepsof fabricating an organic EL device in accordance with the embodiment10.

[0127] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film acted as the anode 2. Then, a thinfilm was formed as the red light emitting layer 4 on the anode 2 by athickness of 40 nm by spin coating in which there was used chloroformsolution containing the compound X3 and N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] at a mol ratio of 1:10.Then, a film composed of triazole derivative [10] was formed as theelectron transporting layer 5 on the red light emitting layer 4 by athickness of 50 nm by vacuum evaporation. Then, a magnesium-silver alloyfilm was formed as the cathode 6 on the electron transporting layer 5 bya thickness of 200 nm by vacuum evaporation. Thus, there was completedthe organic EL device in accordance with the embodiment 10.

[0128] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 870 cd/m².

[Embodiment 11]

[0129]FIG. 4 illustrates a cross-section of an organic EL device inaccordance with the embodiment 11. The organic EL device in accordancewith the embodiment 11 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3 and a red light emitting layer 4 both sandwichedbetween the anode 2 and the cathode 6.

[0130] The organic EL device in accordance with the embodiment 11 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a film composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, a film was formed as the red light emitting layer 4on the hole transporting layer 3 by a thickness of 50 nm by vacuumco-evaporation. This film was composed of the quinolinol family metalcomplex [11] and the compound X3 at a weight ratio of 20:1. Then, a filmcomposed of magnesium-silver alloy was formed as the cathode 6 on thered light emitting layer 4 by a thickness of 200 nm by vacuumevaporation. Thus, there was completed the organic EL device inaccordance with the embodiment 11.

[0131] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 700 cd/m².

[Embodiment 12]

[0132] The same steps as the steps carried out in the above-mentionedembodiment 11 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02], and that the red lightemitting layer 4 was formed of the quinolinol family metal complex [13]and the compound X3 at a weight ratio of 20:1 by vacuum co-evaporation,to thereby fabricate an organic EL device in accordance with embodiment12.

[0133] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 860 cd/m².

[Embodiment 13]

[0134] The same steps as the steps carried out in the above-mentionedembodiment 11 were carried out except that the hole transporting layer 3was composed of the compound X3, and that the red light emitting layer 4was composed of the quinolinol family metal complex [13], to therebyfabricate an organic EL device in accordance with embodiment 13.

[0135] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 720 cd/m².

[0136] Hereinbelow are explained embodiments of an organic EL deviceincluding an organic layer containing a compound represented with thechemical formula C2.

[Synthesis Example 1] Synthesis of Compound Y1 (bisanthrene)

[0137] There was carried out cyclization in a conventional manner,employing 9,10,9′,10′-tetrahydrobisansryl with iodine being used as acatalyst, to thereby obtain bisanthrene.

[Synthesis Example 2] Synthesis of Compound Y2(4-di-p-tolylaminobisanthrene)

[0138] First, bisanthrene was dissolved in chloroform to thereby havefirst solution. Then, chloroform solution in which one equivalent ofN-bromosuccinimide was dissolved was added to the first solution, tothereby have second solution. The second solution stood still forreaction at a room temperature for four hours. Then, the resultant wasrefined in a conventional manner to thereby have 4-bromobisanthrene.

[0139] Then, di-p-tolylamine, potassium carbonate, and copper powderwere mixed to the thus obtained 4-bromobisanthrene. The mixture stoodstill for reaction at 200 degrees centigrade for 30 hours. After theresultant solution was diluted with water, reactant was extracted bychloroform. Thereafter, the thus obtained reactant was refined in aconventional manner to thereby obtain 4-di-p-tolylaminobisanthrene.

[Synthesis Example 3] Synthesis of Compound Y3(4,11-bis(di-p-tolylamino) bisanthrene)

[0140] First, bisanthrene was dissolved in chloroform to thereby havefirst solution. Then, chloroform solution in which two equivalents ofN-bromosuccinimide was dissolved was added to the first solution, tothereby have second solution. The second solution stood still forreaction at a room temperature for four hours. Then, the resultant wasrefined in a conventional manner to thereby have4,11-dibromobisanthrene.

[0141] Then, two equivalents of di-p-tolylamine, potassium carbonate,and copper powder were mixed to the thus obtained4,11-dibromobisanthrene. The mixture stood still for reaction at 200degrees centigrade for 30 hours. After the resultant solution wasdiluted with water, reactant was extracted by chloroform. Thereafter,the thus obtained reactant was refined in a conventional manner tothereby obtain 4,11-bis(di-p-tolylamino)bisanthrene.

[Synthesis Example 4] Synthesis of Compound Y4(4,11-bis(4-(4-methylphenylvinyl) phenyl-p-tolylamino)bisanthrene)

[0142] First, bisanthrene was dissolved in chloroform to thereby havefirst solution. Then, chloroform solution in which two equivalents ofN-bromosuccinimide was dissolved was added to the first solution, tothereby have second solution. The second solution stood still forreaction at a room temperature for four hours. Then, the resultant wasrefined in a conventional manner to thereby have4,11-dibromobisanthrene.

[0143] Then, two equivalents of phenyl-p-tolylamine, potassiumcarbonate, and copper powder were mixed to the thus obtained4,11-dibromobisanthrene. The mixture stood still for reaction at 200degrees centigrade for 30 hours. After the resultant solution wasdiluted with water, reactant was extracted by chloroform. Thereafter,the thus obtained reactant was refined in a conventional manner tothereby obtain 4,11-bis(phenyl-p-tolylamino)bisanthrene.

[0144] The thus obtained 4,11-bis(phenyl-p-tolylamino)bisanthrene,pmethylbenzylphosphonic acid diethylester, and hydrogenated sodium werereacted with one another a day in dimethylsulfoxyde. The reactant liquidwas poured into water with ice, and then, reactant was extracted bychloroform. Then, the resultant was refined in a conventional manner tothereby have4,11-bis(4-(4-methylphenylvinyl)phenyl-p-tolylamino)bisanthrene.

[Synthesis Example 5] Synthesis of Compound Y5(4,11-diphenylbisanthrene)

[0145] The same steps as the steps carried out in the above-mentionedSynthesis Example 1 were carried out except that10,10′-diphenyl-9,10,9′,10′-tetrahydrobisansryl was used in place of9,10,9′,10′-tetrahydrobisansryl, to thereby obtain4,11-diphenylbisanthrene.

[0146] In the later mentioned embodiments 1 to 14, a red light emittinglayer includes the compound represented with the chemical formula C2. Inthe embodiments 15 to 17, a red light emitting layer includes a thinfilm composed of both the compound represented with the chemical formulaC2 and a hole transporting material. In the embodiments 18 and 19, a redlight emitting layer includes a thin film composed of both the compoundrepresented with the chemical formula C2 and an electron transportingmaterial. In the embodiments 20 to 23, a hole transporting layerincludes the compound represented with the chemical formula C2.

[Embodiment 1]

[0147] An organic EL device in accordance with the embodiment 1 has across-section as illustrated in FIG. 1. That is, the organic EL devicein accordance with the embodiment 1 is comprised of a glass substrate 1,an anode 2 and a cathode 6 formed on the glass substrate 1, and a redlight emitting layer 4 sandwiched between the anode 2 and the cathode 6.

[0148] The organic EL device in accordance with the embodiment 1 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, the red light emitting layer 4 composed of theabove-mentioned compound Y1 was formed on the anode 2 by a thickness of40 nm by vacuum evaporation. Then, a magnesium-silver alloy film wasformed as the cathode 6 on the red light emitting layer 4 by a thicknessof 200 nm by vacuum evaporation. Thus, there was completed the organicEL device in accordance with the embodiment 1.

[0149] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 50 cd/m².

[Embodiment 2]

[0150] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Y2, to thereby fabricate an organic ELdevice in accordance with embodiment 2.

[0151] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 60 cd/m².

[Embodiment 3]

[0152] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Y3, to thereby fabricate an organic ELdevice in accordance with embodiment 3.

[0153] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 80 cd/m².

[Embodiment 4]

[0154] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Y4, to thereby fabricate an organic ELdevice in accordance with embodiment 4.

[0155] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 100 cd/m².

[Embodiment 5]

[0156] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Y5, to thereby fabricate an organic ELdevice in accordance with embodiment 5.

[0157] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 40 cd/m².

[Embodiment 6]

[0158] An organic EL device in accordance with the embodiment 6 has thesame cross-section as the cross-section of the organic EL device inaccordance with the embodiment 1, illustrated in FIG. 1. Hereinbelow areexplained steps of fabricating the organic EL device in accordance withthe embodiment 6.

[0159] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film was used as the anode 2. Then, thered light emitting layer 4 was formed on the anode 2 by a thickness of40 nm by spin coating in which chloroform solution containing theabove-mentioned compound Y4 dissolved therein was used. Then, amagnesium-silver alloy film was formed as the cathode 6 on the red lightemitting layer 4 by a thickness of 200 nm by vacuum evaporation. Thus,there was completed the organic EL device in accordance with theembodiment 6.

[0160] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 70 cd/m².

[Embodiment 7]

[0161]FIG. 2 illustrates a cross-section of an organic EL device inaccordance with the embodiment 7. The organic EL device in accordancewith the embodiment 7 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3, a red light emitting layer 4, and an electrontransporting layer 5 all sandwiched between the anode 2 and the cathode6.

[0162] The organic EL device in accordance with the embodiment 7 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, a film composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, the red light emitting layer 4 composed of theabove-mentioned compound Y1 was formed on the hole transporting layer 3by a thickness of 40 nm by vacuum evaporation. Then, a film composed of2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole [07] was formed asthe electron transporting layer 5 on the red light emitting layer 4 by athickness of 20 nm by vacuum evaporation. Then, a film composed ofmagnesium-silver alloy was formed as the cathode 6 on the electrontransporting layer 5 by a thickness of 200 nm by vacuum evaporation.Thus, there was completed the organic EL device in accordance with theembodiment 7.

[0163] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 700 cd/m².

[Embodiment 8]

[0164] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Y2, to thereby fabricate an organic ELdevice in accordance with embodiment 8.

[0165] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1000 cd/m².

[Embodiment 9]

[0166] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Y3, to thereby fabricate an organic ELdevice in accordance with embodiment 8.

[0167] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1500 cd/m².

[Embodiment 10]

[0168] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Y4, to thereby fabricate an organic ELdevice in accordance with embodiment 10.

[0169] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 2500 cd/m².

[Embodiment 11]

[0170] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Y5, to thereby fabricate an organic ELdevice in accordance with embodiment 11.

[0171] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 1400 cd/m².

[Embodiment 12]

[0172] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03], and that the electrontransporting layer 5 was composed ofbis{2-(4-t-butylphenyl)-1,3,4-oxadiazole}-m-phenylene [08], to therebyfabricate an organic EL device in accordance with embodiment 12.

[0173] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 1500 cd/m².

[Embodiment 13]

[0174] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [04], thatthe red light emitting layer 4 was composed of the compound Y3, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [11], to thereby fabricate an organic ELdevice in accordance with embodiment 13.

[0175] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 2000 cd/m².

[Embodiment 14]

[0176] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [05], thatthe red light emitting layer 4 was composed of the compound Y4, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [12], to thereby fabricate an organic ELdevice in accordance with embodiment 14.

[0177] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 3000 cd/m².

[Embodiment 15]

[0178]FIG. 3 illustrates a cross-section of an organic EL device inaccordance with the embodiment 15. The organic EL device in accordancewith the embodiment 15 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a red lightemitting layer 4 and an electron transporting layer 5 both sandwichedbetween the anode 2 and the cathode 6.

[0179] The organic EL device in accordance with the embodiment 15 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, a thin film was formed as the red light emittinglayer 4 on the anode 2 by a thickness of 50 nm by co-evaporation. Thisthin film was composed of both N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] and the above-mentionedcompound Y1 at a weight ratio of 1:10. Then, a film composed of triazolederivative [09] was formed as the electron transporting layer 5 on thered light emitting layer 4 by a thickness of 50 nm by vacuumevaporation. Then, a magnesium-silver alloy film was formed as thecathode 6 on the electron transporting layer 5 by a thickness of 200 nmby vacuum evaporation. Thus, there was completed the organic EL devicein accordance with the embodiment 15.

[0180] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 700 cd/m².

[Embodiment 16]

[0181] The same steps as the steps carried out in the above-mentionedembodiment 15 were carried out except that the compound Y3 was used inplace of the compound Y1, to thereby fabricate an organic EL device inaccordance with embodiment 16.

[0182] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 1700 cd/m².

[Embodiment 17]

[0183] An organic EL device in accordance with the embodiment 17 has thesame cross-section as the cross-section of the organic EL device inaccordance with the embodiment 15, illustrated in FIG. 3. Hereinbeloware explained steps of fabricating the organic EL device in accordancewith the embodiment 17.

[0184] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film was used as the anode 2. Then, athin film was formed as the red light emitting layer 4 on the anode 2 bya thickness of 40 nm by spin coating in which chloroform solutioncontaining the above-mentioned compound Y2 and N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] at a mol ratio of 1:10 wasused. Then, a film composed of triazole derivative [10] was formed asthe electron transporting layer 5 on the red light emitting layer 4 by athickness of 50 nm by vacuum evaporation. Then, a magnesium-silver alloyfilm was formed as the cathode 6 on the electron transporting layer 5 bya thickness of 200 nm by vacuum evaporation. Thus, there was completedthe organic EL device in accordance with the embodiment 17.

[0185] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 1600 cd/m².

[Embodiment 18]

[0186]FIG. 4 illustrates a cross-section of an organic EL device inaccordance with the embodiment 18. The organic EL device in accordancewith the embodiment 18 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3 and a red light emitting layer 4 both sandwichedbetween the anode 2 and the cathode 6.

[0187] The organic EL device in accordance with the embodiment 18 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a film composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, a film was formed as the red light emitting layer 4on the hole transporting layer 3 by a thickness of 50 nm by vacuumco-evaporation. This film was composed of the quinolinol family metalcomplex [11] and the compound Y1 at a weight ratio of 20:1. Then, a filmcomposed of magnesium-silver alloy was formed as the cathode 6 on thered light emitting layer 4 by a thickness of 200 nm by vacuumevaporation. Thus, there was completed the organic EL device inaccordance with the embodiment 18.

[0188] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 1500 cd/m².

[Embodiment 19]

[0189] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the red light emitting layer4 was comprised of a 50 nm-thick film containing the quinolinol familymetal complex [11] and the above-mentioned compound Y4, and formed byvacuum co-evaporation, to thereby fabricate an organic EL device inaccordance with embodiment 19.

[0190] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 2200 cd/m².

[Embodiment 20]

[0191] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine [02], and that the redlight emitting layer 4 was comprised of a film containing both thequinolinol family metal complex [13] and the above-mentioned compound Y4at a weight ratio of 20:1, and formed by vacuum co-evaporation, tothereby fabricate an organic EL device in accordance with embodiment 20.

[0192] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 1600 cd/m².

[Embodiment 21]

[0193] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the compound Y2 was used inplace of the compound Y1 for forming the hole transporting layer 3, andthat the quinolinol family metal complex [13] was used in place of thequinolinol family metal complex [11] for forming the red light emittinglayer 4, to thereby fabricate an organic EL device in accordance withembodiment 21.

[0194] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 500 cd/m².

[Embodiment 22]

[0195] The same steps as the steps carried out in the above-mentionedembodiment 21 were carried out except that the hole transporting layer 3was composed of the above-mentioned compound Y3, to thereby fabricate anorganic EL device in accordance with embodiment 22.

[0196] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 700 cd/m².

[Embodiment 23]

[0197] The same steps as the steps carried out in the above-mentionedembodiment 21 were carried out except that the hole transporting layer 3was composed of the above-mentioned compound Y4, to thereby fabricate anorganic EL device in accordance with embodiment 23.

[0198] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light emission of 900 cd/m².

[0199] Hereinbelow are explained embodiments of an organic EL deviceincluding an organic layer containing a compound represented with thechemical formula C3.

[Synthesis Example 1] Synthesis of Compound Z1 (benzo [a] perylene)

[0200] In accordance with a conventional manner,7,14-dioxo-7,14-dihydrobenzo [a] perylene was treated in zinc powdercontained in pyridine, and then, treated in 80% acetic acid. Theresultant was refined in a conventional manner to thereby obtain atarget material, benzo [a] perylene.

[Synthesis Example 2] Synthesis of Compound Z2 (di-p-tolylaminobenzo [a]perylene)

[0201] Benzo [a] perylene was dissolved in carbon tetrachloride. Oneequivalent of bromine was mixed to the thus obtained solution whilebeing cooled. The mixture stood still for reaction for four hours. Then,the mixture was refined in a conventional manner to thereby obtainbromobenzo [a] perylene.

[0202] Then, di-p-tolylamine, potassium carbonate, and copper power wereadded to the thus obtained bromobenzo [a] perylene. This mixture stoodstill for reaction at 200 degrees centigrade for thirty hours. Afterreactant solution was diluted with water, reactant was extracted bychloroform. Thereafter, the reactant was refined in a conventionalmanner to thereby obtain di-p-tolylaminobenzo [a] perylene.

[Synthesis Example 3] Synthesis of Compound Z3 (bis (di-p-tolylamino)benzo [a] perylene)

[0203] Benzo [a] perylene was dissolved in carbon tetrachloride. Twoequivalents of bromine was mixed to the thus obtained solution whilebeing cooled. The mixture stood still for reaction for four hours. Then,the mixture was refined in a conventional manner to thereby obtaindibromobenzo [a] perylene.

[0204] Then, two equivalents of di-p-tolylamine, potassium carbonate,and copper power were added to the thus obtained dibromobenzo [a]perylene. This mixture stood still for reaction at 200 degreescentigrade for thirty hours. After reactant solution was diluted withwater, reactant was extracted by chloroform. Thereafter, the reactantwas refined in a conventional manner to thereby obtain bis(di-p-tolylamino) benzo [a] perylene.

[Synthesis Example 4] Synthesis of Compound Z4 ((4-(4-methylphenylvinyl)phenyl-p-tolylamino) benzo [a] perylene)

[0205] First, there was obtained bromobenzo [a] perylene in the samemanner as that of the above-mentioned Synthesis Example 3. Then, oneequivalent of phenyl-p-tolylamine, potassium carbonate, and copper powerwere added to the thus obtained bromobenzo [a] perylene. This mixturestood still for reaction at 200 degrees centigrade for 30 hours. Afterreactant solution was diluted with water, reactant was extracted bychloroform. Thereafter, the reactant was refined in a conventionalmanner to thereby obtain phenyl-p-tolylaminobenzo [a] perylene.

[0206] The thus obtained phenyl-p-tolylaminobenzo [a] perylene wasdissolved in toluene, to which oxy phosphorus chloride was furtheradded. The thus obtained solution was stirred at a room temperature.Then, N-methylformanilide was dropped into the solution, and then, thesolution was stirred at 50 degrees centigrade for 5 hours. Afterreaction was completed, the resultant was poured into cold water, andthen, transferred into a separatory funnel. Then, the resultant toluenelayer was washed with water a couple of times until the toluene layerbecame neutral.

[0207] After the resultant was dried with magnesium sulfate, solvent wasremoved. Then, the resultant was refined in a conventional manner tothereby obtain N-p-formylphenyl-N-tolylaminobenzo [a] perylene. The thusobtained N-p-formylphenyl-N-tolylaminobenzo [a] perylene, p-methylbenzylphosphonic acid diethylester, and hydrogenated sodium were mixed withone another, and stood still for reaction a day in dimethylsufoxyd.After reactant solution was poured into cold water, reactant wasextracted by chloroform. Thereafter, the reactant was refined in aconventional manner to thereby obtain 4-(4-methylphenylvinyl)phenyl-p-tolylamino) benzo [a] perylene.

[Synthesis Example 5] Synthesis of Compound Z5(bis(4-(4-methylphenylvinyl) phenyl-p-tolylamino) benzo [a] perylene)

[0208] The same steps as the steps carried out in the above-mentionedSynthesis Example 4 were carried out except that dibromobenzo [a]perylene was used in place of bromobenzo [a] perylene, and that twoequivalents of phenyl-p-tolylamine was used in place of one equivalentof the same, to thereby obtain bis (4-(4-methylphenylvinyl)phenyl-p-tolylamino) benzo [a] perylene.

[0209] In the later mentioned embodiments 1 to 14, a red light emittinglayer includes the benzoperylene compound represented with the chemicalformula C3. In the embodiments 15 to 17, a red light emitting layerincludes a thin film composed of both the benzoperylene compoundrepresented with the chemical formula C3 and a hole transportingmaterial. In the embodiments 18 to 20, a red light emitting layerincludes a thin film composed of both the compound represented with thechemical formula C3 and an electron transporting material. In theembodiments 21 and 22, a hole transporting layer includes a thin filmcomposed of both the compound represented with the chemical formula C3and an electron transporting material. In the embodiment 23, an electrontransporting layer includes a thin film composed of both the compoundrepresented with the chemical formula C3 and an electron transportingmaterial.

[Embodiment 1]

[0210] An organic EL device in accordance with the embodiment 1 has across-section as illustrated in FIG. 1. That is, the organic EL devicein accordance with the embodiment 1 is comprised of a glass substrate 1,an anode 2 and a cathode 6 formed on the glass substrate 1, and a redlight emitting layer 4 sandwiched between the anode 2 and the cathode 6.

[0211] The organic EL device in accordance with the embodiment 1 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, the red light emitting layer 4 composed of theabove-mentioned compound Z1 was formed on the anode 2 by a thickness of40 nm by vacuum evaporation. Then, a magnesium-silver alloy film wasformed as the cathode 6 on the red light emitting layer 4 by a thicknessof 200 nm by vacuum evaporation. Thus, there was completed the organicEL device in accordance with the embodiment 1.

[0212] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 30 cd/m².

[Embodiment 2]

[0213] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Z2, to thereby fabricate an organic ELdevice in accordance with embodiment 2.

[0214] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 70 cd/m².

[Embodiment 3]

[0215] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Z3, to thereby fabricate an organic ELdevice in accordance with embodiment 3.

[0216] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 100 cd/m².

[Embodiment 4]

[0217] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Z4, to thereby fabricate an organic ELdevice in accordance with embodiment 4.

[0218] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 120 cd/m².

[Embodiment 5]

[0219] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound Z5, to thereby fabricate an organic ELdevice in accordance with embodiment 5.

[0220] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 140 cd/m².

[Embodiment 6]

[0221] An organic EL device in accordance with the embodiment 6 has thesame cross-section as that of the organic EL device in accordance withthe embodiment 1, illustrated in FIG. 1. Hereinbelow is explained stepsof fabricating an organic EL device in accordance with the embodiment 6.

[0222] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film acted as the anode 2. Then, the redlight emitting layer 4 was formed on the anode 2 by a thickness of 40 nmby spin coating in which chloroform solution containing theabove-mentioned compound Z5 dissolved therein was used. Then, amagnesium-silver alloy film was formed as the cathode 6 on the red lightemitting layer 4 by a thickness of 200 nm by vacuum evaporation. Thus,there was completed the organic EL device in accordance with theembodiment 6.

[0223] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 70 cd/m².

[Embodiment 7]

[0224]FIG. 2 illustrates a cross-section of an organic EL device inaccordance with the embodiment 7. The organic EL device in accordancewith the embodiment 7 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3, a red light emitting layer 4, and an electrontransporting layer 5 all sandwiched between the anode 2 and the cathode6.

[0225] The organic EL device in accordance with the embodiment 7 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a film composed ofN,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02]was formed as the hole transporting layer 3 on the anode 2 by athickness of 50 nm by vacuum evaporation. Then, the red light emittinglayer 4 composed of the above-mentioned compound Z1 was formed on thehole transporting layer 3 by a thickness of 40 nm by vacuum evaporation.Then, a film composed of2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole [07] was formed asthe electron transporting layer 5 on the red light emitting layer 4 by athickness of 20 nm by vacuum evaporation. Then, a film composed ofmagnesium-silver alloy was formed as the cathode 6 on the electrontransporting layer 5 by a thickness of 200 nm by vacuum evaporation.Thus, there was completed the organic EL device in accordance with theembodiment 7.

[0226] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 400 cd/m².

[Embodiment 8]

[0227] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Z2, to thereby fabricate an organic ELdevice in accordance with embodiment 8.

[0228] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1200 cd/m².

[Embodiment 9]

[0229] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Z3, to thereby fabricate an organic ELdevice in accordance with embodiment 9.

[0230] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1800 cd/m².

[Embodiment 10]

[0231] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Z4, to thereby fabricate an organic ELdevice in accordance with embodiment 10.

[0232] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2000 cd/m².

[Embodiment 11]

[0233] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound Z5, to thereby fabricate an organic ELdevice in accordance with embodiment 11.

[0234] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2500 cd/m².

[Embodiment 12]

[0235] The same steps as the steps carried out in the above-mentionedembodiment 8 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03], and that the electrontransporting layer 5 was composed ofbis{2-(4-t-butylphenyl)-1,3,4-oxadiazole}-m-phenylene [08], to therebyfabricate an organic EL device in accordance with embodiment 12.

[0236] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1700 cd/m².

[Embodiment 13]

[0237] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [04], thatthe red light emitting layer 4 was composed of the compound Z3, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [11], to thereby fabricate an organic ELdevice in accordance with embodiment 13.

[0238] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2200 cd/m².

[Embodiment 14]

[0239] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [05], thatthe red light emitting layer 4 was composed of the compound Z5, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [12], to thereby fabricate an organic ELdevice in accordance with embodiment 14.

[0240] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 4000 cd/m².

[Embodiment 15]

[0241]FIG. 3 illustrates a cross-section of an organic EL device inaccordance with the embodiment 15. The organic EL device in accordancewith the embodiment 15 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a red lightemitting layer 4 and an electron transporting layer 5 both sandwichedbetween the anode 2 and the cathode 6.

[0242] The organic EL device in accordance with the embodiment 15 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a thin film was formed as the red light emittinglayer 4 on the anode 2 by a thickness of 50 nm by co-evaporation. Thisthin film was composed of both N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] and the above-mentionedcompound Z2 at a weight ratio of 1:10. Then, a film composed of triazolederivative [09] was formed as the electron transporting layer 5 on thered light emitting layer 4 by a thickness of 50 nm by vacuumevaporation. Then, a magnesium-silver alloy film was formed as thecathode 6 on the electron transporting layer 5 by a thickness of 200 nmby vacuum evaporation. Thus, there was completed the organic EL devicein accordance with the embodiment 15.

[0243] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 700 cd/m².

[Embodiment 16]

[0244] The same steps as the steps carried out in the above-mentionedembodiment 15 were carried out except that the red light emitting layer4 was composed of the compound Z5 in place of the compound Z2, tothereby fabricate an organic EL device in accordance with embodiment 16.

[0245] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2000 cd/m².

[Embodiment 17]

[0246] An organic EL device in accordance with the embodiment 17 has thesame cross-section as that of the organic EL device in accordance withthe embodiment 15, illustrated in FIG. 3. Hereinbelow is explained stepsof fabricating an organic EL device in accordance with the embodiment17.

[0247] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film was used as the anode 2. Then, athin film was formed as the red light emitting layer 4 on the anode 2 bya thickness of 40 nm by spin coating in which there was used chloroformsolution containing the compound Z5 and N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] at a mol ratio of 1:10.Then, a film composed of triazole derivative [10] was formed as theelectron transporting layer 5 on the red light emitting layer 4 by athickness of 50 nm by vacuum evaporation. Then, a magnesium-silver alloyfilm was formed as the cathode 6 on the electron transporting layer 5 bya thickness of 200 nm by vacuum evaporation. Thus, there was completedthe organic EL device in accordance with the embodiment 17.

[0248] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 900 cd/m².

[Embodiment 18]

[0249]FIG. 4 illustrates a cross-section of an organic EL device inaccordance with the embodiment 18. The organic EL device in accordancewith the embodiment 18 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3 and a red light emitting layer 4 both sandwichedbetween the anode 2 and the cathode 6.

[0250] The organic EL device in accordance with the embodiment 18 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, a film composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, a film was formed as the red light emitting layer 4on the hole transporting layer 3 by a thickness of 50 nm by vacuumco-evaporation. This film was composed of the quinolinol family metalcomplex [11] and the compound Z3 at a weight ratio of 20:1. Then, a filmcomposed of magnesium-silver alloy was formed as the cathode 6 on thered light emitting layer 4 by a thickness of 200 nm by vacuumevaporation. Thus, there was completed the organic EL device inaccordance with the embodiment 18.

[0251] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1400 cd/m².

[Embodiment 19]

[0252] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the red light emitting layer4 was formed of the quinolinol family metal complex [11] and thecompound Z5 at a weight ratio of 20:1 by vacuum co-evaporation, tothereby fabricate an organic EL device in accordance with embodiment 19.

[0253] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2000 cd/m².

[Embodiment 20]

[0254] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02], and that the red lightemitting layer 4 was formed of the quinolinol family metal complex [13]and the compound Z5 at a weight ratio of 20:1 by vacuum co-evaporation,to thereby fabricate an organic EL device in accordance with embodiment20.

[0255] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1800 cd/m².

[Embodiment 21]

[0256] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the compound Z4, and that the red light emitting layer 4was composed of the quinolinol family metal complex [13], to therebyfabricate an organic EL device in accordance with embodiment 21.

[0257] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 500 cd/m².

[Embodiment 22]

[0258] The same steps as the steps carried out in the above-mentionedembodiment 21 were carried out except that the hole transporting layer 3was composed of the compound Z5, to thereby fabricate an organic ELdevice in accordance with embodiment 22.

[0259] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 700 cd/m².

[Embodiment 23]

[0260] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the electron transportinglayer 5 was composed of the compound Z1, and that the red light emittinglayer 4 was composed of the quinolinol family metal complex [11], tothereby fabricate an organic EL device in accordance with embodiment 23.

[0261] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 700 cd/m².

[0262] Hereinbelow are explained embodiments of an organic EL deviceincluding an organic layer containing a compound represented with thechemical formula C4.

[Synthesis Example 1] Synthesis of Compound W1 (terylene)

[0263] In a conventional manner, 1,4-di-1-naphthylnaphthalene wasgradually added to a liquid obtained by heating aluminum chloride andsodium chloride at 180 degrees centigrade to thereby melt. The obtainedsolution was stirred while heated. After reaction was completed,reactant solution was poured into hydrochloric acid. The reactant wasfiltered and washed with hot water to thereby obtain roughly refinedterylene. Then, the thus obtained roughly refined terylene was refinedin a conventional manner to thereby obtain a target material, terylene.

[Synthesis Example 2] Synthesis of Compound W2 (di-p-tolylaminoterylene)

[0264] Terylene was dissolved in carbon tetrachloride. One equivalent ofbromine was mixed to the thus obtained solution while being cooled. Themixture stood still for reaction for 4 hours. Then, the mixture wasrefined in a conventional manner to thereby obtain bromoterylene.

[0265] Then, di-p-tolylamine, potassium carbonate, and copper power wereadded to the thus obtained bromoterylene. This mixture stood still forreaction at 200 degrees centigrade for 30 hours. After reactant solutionwas diluted with water, reactant was extracted by chloroform.Thereafter, the reactant was refined in a conventional manner to therebyobtain di-p-tolylaminoterylene.

[Synthesis Example 3] Synthesis of Compound W3 (bis (di-p-tolylamino)terylene)

[0266] Terylene was dissolved in carbon tetrachloride. Two equivalentsof bromine were mixed to the thus obtained solution while being cooled.The mixture stood still for reaction for 4 hours. Then, the mixture wasrefined in a conventional manner to thereby obtain dibromoterylene.

[0267] Then, two equivalents of di-p-tolylamine, potassium carbonate,and copper power were added to the thus obtained dibromoterylene. Thismixture stood still for reaction at 200 degrees centigrade for 30 hours.After reactant solution was diluted with water, reactant was extractedby chloroform. Thereafter, the reactant was refined in a conventionalmanner to thereby obtain bis (di-p-tolylamino) terylene.

[Synthesis Example 4] Synthesis of Compound W4 ((4-(4-methylphenylvinyl)phenyl-p-tolylamino)terylene)

[0268] First, there was obtained bromoterylene in the same manner asthat of the above-mentioned Synthesis Example 3. Then, one equivalent ofphenyl-p-tolylamine, potassium carbonate, and copper power were added tothe thus obtained bromoterylene. This mixture stood still for reactionat 200 degrees centigrade for 30 hours. After reactant solution wasdiluted with water, reactant was extracted by chloroform. Thereafter,the reactant was refined in a conventional manner to thereby obtainphenyl-p-tolylaminoterylene.

[0269] The thus obtained phenyl-p-tolylaminoterylene was dissolved intoluene, to which oxy phosphorus chloride was further added. Theresultant solution was stirred at a room temperature. Then,N-methylformanilide was dropped into the solution, and then, thesolution was stirred at 50 degrees centigrade for 5 hours. Afterreaction was completed, the resultant was poured into cold water, andthen, transferred into a separatory funnel. Then, the resultant toluenelayer was washed with water a couple of times until the toluene layerbecame neutral.

[0270] After the resultant was dried with magnesium sulfate, solvent wasremoved. Then, the resultant was refined in a conventional manner tothereby obtain N-p-formylphenyl-N-tolylaminoterylene. The thus obtainedN-p-formylphenyl-N-tolylaminoterylene, p-methylbenzyl phosphonic aciddiethylester, and hydrogenated sodium were mixed with one another, andstood still for reaction a day in dimethylsufoxyd. After reactantsolution was poured into cold water, reactant was extracted bychloroform. Thereafter, the reactant was refined in a conventionalmanner to thereby obtain 4-(4-methylphenylvinyl) phenyl-p-tolylamino)terylene.

[Synthesis Example 5] Synthesis of Compound W5(bis(4-(4-methylphenylvinyl) phenyl-p-tolylamino)terylene)

[0271] The same steps as the steps carried out in the above-mentionedSynthesis Example 4 were carried out except that dibromoterylene wasused in place of bromoterylene, and that two equivalents ofphenyl-p-tolylamine was used in place of one equivalent of the same, tothereby obtain bis (4-(4-methylphenylvinyl)phenyl-p-tolylamino)terylene.

[0272] In the later mentioned embodiments 1 to 14, a red light emittinglayer includes the compound represented with the chemical formula C4. Inthe embodiments 15 to 17, a red light emitting layer includes a thinfilm composed of both the compound represented with the chemical formulaC4 and a hole transporting material. In the embodiments 18 to 20, a redlight emitting layer includes a thin film composed of both the compoundrepresented with the chemical formula C4 and an electron transportingmaterial. In the embodiments 21 and 22, a hole transporting layerincludes a thin film composed of the compound represented with thechemical formula C4. In the embodiment 23, an electron transportinglayer includes a thin film composed of the compound represented with thechemical formula C4.

[Embodiment 1]

[0273] An organic EL device in accordance with the embodiment 1 has across-section as illustrated in FIG. 1. That is, the organic EL devicein accordance with the embodiment 1 is comprised of a glass substrate 1,an anode 2 and a cathode 6 formed on the glass substrate 1, and a redlight emitting layer 4 sandwiched between the anode 2 and the cathode 6.

[0274] The organic EL device in accordance with the embodiment 1 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, the red light emitting layer 4 composed of theabove-mentioned compound W1 was formed on the anode 2 by a thickness of40 nm by vacuum evaporation. Then, a magnesium-silver alloy film wasformed as the cathode 6 on the red light emitting layer 4 by a thicknessof 200 nm by vacuum evaporation. Thus, there was completed the organicEL device in accordance with the embodiment 1.

[0275] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 40 cd/m².

[Embodiment 2]

[0276] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound W2, to thereby fabricate an organic ELdevice in accordance with embodiment 2.

[0277] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 60 cd/m².

[Embodiment 3]

[0278] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound W3, to thereby fabricate an organic ELdevice in accordance with embodiment 3.

[0279] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 90 cd/m².

[Embodiment 4]

[0280] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound W4, to thereby fabricate an organic ELdevice in accordance with embodiment 4.

[0281] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 110 cd/m².

[Embodiment 5]

[0282] The same steps as the steps carried out in the above-mentionedembodiment 1 were carried out except that the red light emitting layer 4was composed of the compound W5, to thereby fabricate an organic ELdevice in accordance with embodiment 5.

[0283] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 130 cd/m².

[Embodiment 6]

[0284] An organic EL device in accordance with the embodiment 6 has thesame cross-section as that of the organic EL device in accordance withthe embodiment 1, illustrated in FIG. 1. Hereinbelow is explained stepsof fabricating an organic EL device in accordance with the embodiment 6.

[0285] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film acted as the anode 2. Then, the redlight emitting layer 4 was formed on the anode 2 by a thickness of 40 nmby spin coating in which chloroform solution containing theabove-mentioned compound W5 dissolved therein was used. Then, amagnesium-silver alloy film was formed as the cathode 6 on the red lightemitting layer 4 by a thickness of 200 nm by vacuum evaporation. Thus,there was completed the organic EL device in accordance with theembodiment 6.

[0286] A direct current voltage of 5V was applied across the anode 2 andthe cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 60 cd/m².

[Embodiment 7]

[0287]FIG. 2 illustrates a cross-section of an organic EL device inaccordance with the embodiment 7. The organic EL device in accordancewith the embodiment 7 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3, a red light emitting layer 4, and an electrontransporting layer 5 all sandwiched between the anode 2 and the cathode6.

[0288] The organic EL device in accordance with the embodiment 7 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a film composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, the red light emitting layer 4 composed of theabove-mentioned compound W1 was formed on the hole transporting layer 3by a thickness of 40 nm by vacuum evaporation. Then, a film composed of2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole [07] was formed asthe electron transporting layer 5 on the red light emitting layer 4 by athickness of 20 nm by vacuum evaporation. Then, a film composed ofmagnesium-silver alloy was formed as the cathode 6 on the electrontransporting layer 5 by a thickness of 200 nm by vacuum evaporation.Thus, there was completed the organic EL device in accordance with theembodiment 7.

[0289] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 350 cd/m².

[Embodiment 8]

[0290] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound W2, to thereby fabricate an organic ELdevice in accordance with embodiment 8.

[0291] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1000 cd/m².

[Embodiment 9]

[0292] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound W3, to thereby fabricate an organic ELdevice in accordance with embodiment 9.

[0293] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1900 cd/m².

[Embodiment 10]

[0294] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound W4, to thereby fabricate an organic ELdevice in accordance with embodiment 10.

[0295] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2010 cd/m².

[Embodiment 11]

[0296] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the red light emitting layer 4was composed of the compound W5, to thereby fabricate an organic ELdevice in accordance with embodiment 11.

[0297] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2470 cd/m².

[Embodiment 12]

[0298] The same steps as the steps carried out in the above-mentionedembodiment 8 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03], and that the electrontransporting layer 5 was composed ofbis{2-(4-t-butylphenyl)-1,3,4-oxadiazole}-m-phenylene [08], to therebyfabricate an organic EL device in accordance with embodiment 12.

[0299] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1850 cd/m².

[Embodiment 13]

[0300] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [04], thatthe red light emitting layer 4 was composed of the compound W3, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [11], to thereby fabricate an organic ELdevice in accordance with embodiment 13.

[0301] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2310 cd/m².

[Embodiment 14]

[0302] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the above-mentioned star burst type molecules [05], thatthe red light emitting layer 4 was composed of the compound W5, and thatthe electron transporting layer 5 was composed of the above-mentionedquinolinol family metal complex [12], to thereby fabricate an organic ELdevice in accordance with embodiment 14.

[0303] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 3960 cd/m².

[Embodiment 15]

[0304]FIG. 3 illustrates a cross-section of an organic EL device inaccordance with the embodiment 15. The organic EL device in accordancewith the embodiment 15 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a red lightemitting layer 4 and an electron transporting layer 5 both sandwichedbetween the anode 2 and the cathode 6.

[0305] The organic EL device in accordance with the embodiment 15 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film acted asthe anode 2. Then, a thin film was formed as the red light emittinglayer 4 on the anode 2 by a thickness of 50 nm by co-evaporation. Thisthin film was composed of both N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] and the above-mentionedcompound W2 at a weight ratio of 1:10. Then, a film composed of triazolederivative [09] was formed as the electron transporting layer 5 on thered light emitting layer 4 by a thickness of 50 nm by vacuumevaporation. Then, a magnesium-silver alloy film was formed as thecathode 6 on the electron transporting layer 5 by a thickness of 200 nmby vacuum evaporation. Thus, there was completed the organic EL devicein accordance with the embodiment 15.

[0306] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 710 cd/m².

[Embodiment 16]

[0307] The same steps as the steps carried out in the above-mentionedembodiment 15 were carried out except that the red light emitting layer4 was composed of the compound W5 in place of the compound W2, tothereby fabricate an organic EL device in accordance with embodiment 16.

[0308] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 2100 cd/m².

[Embodiment 17]

[0309] An organic EL device in accordance with the embodiment 17 has thesame cross-section as that of the organic EL device in accordance withthe embodiment 15, illustrated in FIG. 3. Hereinbelow is explained stepsof fabricating an organic EL device in accordance with the embodiment17.

[0310] First, an ITO film was formed on the glass substrate 1 bysputtering so that the ITO film has a sheet resistance of 20 ohms per aunit area. The thus formed ITO film was used as the anode 2. Then, athin film was formed as the red light emitting layer 4 on the anode 2 bya thickness of 40 nm by spin coating in which there was used chloroformsolution containing the compound W5 and N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] at a mol ratio of 1:10.Then, a film composed of triazole derivative [10] was formed as theelectron transporting layer 5 on the red light emitting layer 4 by athickness of 50 nm by vacuum evaporation. Then, a magnesium-silver alloyfilm was formed as the cathode 6 on the electron transporting layer 5 bya thickness of 200 nm by vacuum evaporation. Thus, there was completedthe organic EL device in accordance with the embodiment 17.

[0311] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 880 cd/m².

[Embodiment 18]

[0312]FIG. 4 illustrates a cross-section of an organic EL device inaccordance with the embodiment 18. The organic EL device in accordancewith the embodiment 18 is comprised of a glass substrate 1, an anode 2and a cathode 6 both formed on the glass substrate 1, and a holetransporting layer 3 and a red light emitting layer 4 both sandwichedbetween the anode 2 and the cathode 6.

[0313] The organic EL device in accordance with the embodiment 18 wasfabricated in the following steps. First, an ITO film was formed on theglass substrate 1 by sputtering so that the ITO film has a sheetresistance of 20 ohms per a unit area. The thus formed ITO film was usedas the anode 2. Then, a film composed of N,N′-diphenyl-N-N-bis(1-naphthyl)-1,1′-biphenyl-4,4′-diamine [03] was formed as the holetransporting layer 3 on the anode 2 by a thickness of 50 nm by vacuumevaporation. Then, a film was formed as the red light emitting layer 4on the hole transporting layer 3 by a thickness of 50 nm by vacuumco-evaporation. This film was composed of the quinolinol family metalcomplex [11] and the compound W3 at a weight ratio of 20:1. Then, a filmcomposed of magnesium-silver alloy was formed as the cathode 6 on thered light emitting layer 4 by a thickness of 200 nm by vacuumevaporation. Thus, there was completed the organic EL device inaccordance with the embodiment 18.

[0314] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1520 cd/m².

[Embodiment 19]

[0315] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the red light emitting layer4 was formed of the quinolinol family metal complex [11] and thecompound W5 at a weight ratio of 20:1 by vacuum co-evaporation, tothereby fabricate an organic EL device in accordance with embodiment 19.

[0316] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1800 cd/m².

[Embodiment 20]

[0317] The same steps as the steps carried out in the above-mentionedembodiment 18 were carried out except that the hole transporting layer 3was composed of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine [02], and that the red lightemitting layer 4 was formed of both the quinolinol family metal complex[13] and the compound W5 at a weight ratio of 20:1 by vacuumco-evaporation, to thereby fabricate an organic EL device in accordancewith embodiment 20.

[0318] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 1640 cd/m².

[Embodiment 21]

[0319] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the hole transporting layer 3was composed of the compound W4, and that the red light emitting layer 4was composed of the quinolinol family metal complex [13], to therebyfabricate an organic EL device in accordance with embodiment 21.

[0320] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 600 cd/m².

[Embodiment 22]

[0321] The same steps as the steps carried out in the above-mentionedembodiment 21 were carried out except that the hole transporting layer 3was composed of the compound W5, to thereby fabricate an organic ELdevice in accordance with embodiment 22.

[0322] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 870 cd/m².

[Embodiment 23]

[0323] The same steps as the steps carried out in the above-mentionedembodiment 7 were carried out except that the electron transportinglayer 5 was composed of the compound W1, and that the red light emittinglayer 4 was composed of the quinolinol family metal complex [11], tothereby fabricate an organic EL device in accordance with embodiment 23.

[0324] A direct current voltage of 10V was applied across the anode 2and the cathode 6 of the thus fabricated organic EL device. As a result,there was obtained red light-emission of 100 cd/m².

[0325] As having been described with reference to the preferredembodiments, the organic EL device in accordance with the presentinvention is designed to include an organic thin layer composed of thecompound represented with the chemical formula C1, C2, C3 or C4, andhence, accomplish red light-emission at a higher brightness than abrightness of conventional organic EL devices.

[0326] While the present invention has been described in connection withcertain preferred embodiments, it is to be understood that the subjectmatter encompassed by way of the present invention is not to be limitedto those specific embodiments. On the contrary, it is intended for thesubject matter of the invention to include all alternatives,modifications and equivalents as can be included within the spirit andscope of the following claims.

[0327] The entire disclosure of Japanese Patent Applications Nos.9-303047, 9-303048, 9-357022, and 10-886 filed on Nov. 5, 1997, Nov. 5,1997, Dec. 25, 1997, and Jan. 6, 1998, respectively, each includingspecification, claims, drawings and summary is incorporated herein byreference in its entirety.

What is claimed is:
 1. An electroluminescent device comprising: (a) ananode; (b) a cathode; and (c) at least one organic layer sandwichedbetween said anode and said cathode, said organic layer including atleast a red light emitting layer, said organic layer containing acompound represented with the chemical formula C1, alone or incombination:

wherein R¹ to R⁴ each independently represents a hydrogen atom, ahydroxyl group, a substituted or unsubstituted amino group, a nitrogroup, a substituted or unsubstituted alkyl group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted cycloalkylgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted aromatic hydrocarbon group, a substituted or unsubstitutedaromatic heterocyclic group, or a substituted or unsubstituted aralkylgroup, wherein at least one of R¹ to R⁴ is a di-aryl amino grouprepresented with —NAr¹Ar² where each of Ar¹ and Ar² independentlyindicates an aryl group having a carbon number of 6 to 20 bothinclusive, wherein R⁵ to R¹² each independently represents a hydrogenatom, a halogen atom, a hydroxyl group, a substituted or unsubstitutedamino group, a nitro group, a cyano group, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aromatichydrocarbon group, a substituted or unsubstituted aromatic heterocyclicgroup, or a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryloxy group, a substituted or unsubstitutedalkoxycarbonyl group, or a carboxyl group, and wherein any two of R¹ toR⁴ except diaryl amino group and R⁵ to R¹² may form a ring.
 2. Theorganic electroluminescent device as set forth in claim 1, wherein eachof said Ar¹ and Ar² includes a substituent.
 3. The organicelectroluminescent device as set forth in claim 1, wherein said organiclayer includes a hole transporting layer containing said compoundrepresented with said chemical formula C1, alone or in combination. 4.The organic electroluminescent device as set forth in claim 1, whereinsaid anode has a work function equal to or greater than 4.5 eV.
 5. Theorganic electroluminescent device as set forth in claim 5, wherein saidcathode has a smaller work function than that of said anode.
 6. Theorganic electroluminescent device as set forth in claim 1, wherein saidorganic layer has a thickness in the range of 1 nanometer to 1micrometer both inclusive.
 7. An electroluminescent device comprising:(a) an anode; (b) a cathode; and (c) at least one organic layersandwiched between said anode and said cathode, said organic layerincluding at least a red light emitting layer, said organic layercontaining a bisanthrene compound represented with the chemical formulaC2, alone or in combination:

wherein R¹ to R¹⁴ each independently represents a hydrogen atom, ahalogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group, and wherein any two of R¹ to R¹⁴ may form a ring.
 8. Theorganic electroluminescent device as set forth in claim 7, wherein saidorganic layer includes a hole transporting layer containing saidcompound represented with said chemical formula C2, alone or incombination.
 9. The organic electroluminescent device as set forth inclaim 7, wherein said organic layer includes an electron transportinglayer containing said compound represented with said chemical formulaC2, alone or in combination.
 10. The organic electroluminescent deviceas set forth in claim 7, wherein said organic layer includes both a holetransporting layer and an electron transporting layer, said electrontransporting layer containing said compound represented with saidchemical formula C2, alone or in combination.
 11. The organicelectroluminescent device as set forth in claim 7, wherein said anodehas a work function equal to or greater than 4.5 eV.
 12. The organicelectroluminescent device as set forth in claim 11, wherein said cathodehas a smaller work function than that of said anode.
 13. The organicelectroluminescent device as set forth in claim 7, wherein said organiclayer has a thickness in the range of 1 nanometer to 1 micrometer bothinclusive.
 14. An electroluminescent device comprising: (a) an anode;(b) a cathode; and (c) at least one organic layer sandwiched betweensaid anode and said cathode, said organic layer including at least a redlight emitting layer, said organic layer containing a benzoperylenecompound represented with the chemical formula C3, alone or incombination:

wherein R¹ to R¹⁴ each independently represents a hydrogen atom, ahalogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group, and wherein any two of R¹ to R¹⁴ may form a ring. 15.The organic electroluminescent device as set forth in claim 14, whereinsaid organic layer includes a hole transporting layer containing saidbenzoperylene compound represented with said chemical formula C3, aloneor in combination.
 16. The organic electroluminescent device as setforth in claim 14, wherein said organic layer includes an electrontransporting layer containing said benzoperylene compound representedwith said chemical formula C3, alone or in combination.
 17. The organicelectroluminescent device as set forth in claim 14, wherein at least oneof R¹ to R¹ ⁴ is a di-aryl amino group represented with —NAr¹Ar² whereeach of Ar¹ and Ar² independently indicates an aryl group having acarbon number of 6 to 20 both inclusive.
 18. The organicelectroluminescent device as set forth in claim 17, wherein said arylgroup has a substituent.
 19. The organic electroluminescent device asset forth in claim 14, wherein at least one of R¹ to R¹ ⁴ is a di-arylamino group represented with —NAr¹Ar² where each of Ar¹ and Ar²independently indicates an aryl group having a carbon number of 6 to 20both inclusive, and at least one of said Ar¹ and Ar² includes asubstituted or unsubstituted styryl group as a substituent.
 20. Theorganic electroluminescent device as set forth in claim 19, wherein saidaryl group has a substituent.
 21. The organic electroluminescent deviceas set forth in claim 14, wherein said anode has a work function equalto or greater than 4.5 eV.
 22. The organic electroluminescent device asset forth in claim 21, wherein said cathode has a smaller work functionthan that of said anode.
 23. The organic electroluminescent device asset forth in claim 14, wherein said organic layer has a thickness in therange of 1 nanometer to 1 micrometer both inclusive.
 24. Anelectroluminescent device comprising: (a) an anode; (b) a cathode; and(c) at least one organic layer sandwiched between said anode and saidcathode, said organic layer including at least a red light emittinglayer, said organic layer containing a terylene compound representedwith the chemical formula C4, alone or in combination:

wherein R¹ to R¹⁶ each independently represents a hydrogen atom, ahalogen atom, a hydroxyl group, a substituted or unsubstituted aminogroup, a nitro group, a cyano group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxygroup, a substituted or unsubstituted aromatic hydrocarbon group, asubstituted or unsubstituted aromatic heterocyclic group, a substitutedor unsubstituted aralkyl group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkoxycarbonyl group, or acarboxyl group, and wherein any two of R¹ to R¹⁸ may form a ring. 25.The organic electroluminescent device as set forth in claim 24, whereinsaid organic layer includes a hole transporting layer containing saidterylene compound represented with said chemical formula C4, alone or incombination.
 26. The organic electroluminescent device as set forth inclaim 24, wherein said organic layer includes an electron transportinglayer containing said terylene compound represented with said chemicalformula C4, alone or in combination.
 27. The organic electroluminescentdevice as set forth in claim 24, wherein at least one of R¹ to R¹⁴ is adi-aryl amino group represented with —NAr¹Ar² where each of Ar¹ and Ar²independently indicates an aryl group having a carbon number of 6 to 20both inclusive.
 28. The organic electroluminescent device as set forthin claim 27, wherein said aryl group has a substituent.
 29. The organicelectroluminescent device as set forth in claim 24, wherein at least oneof R¹ to R¹⁴ is a di-aryl amino group represented with —NAr¹Ar² whereeach of Ar¹ and Ar² independently indicates an aryl group having acarbon number of 6 to 20 both inclusive, and at least one of said Ar¹and Ar² includes a substituted or unsubstituted styryl group as asubstituent.
 30. The organic electroluminescent device as set forth inclaim 29, wherein said aryl group has a substituent.
 31. The organicelectroluminescent device as set forth in claim 24, wherein said anodehas a work function equal to or greater than 4.5 eV.
 32. The organicelectroluminescent device as set forth in claim 31, wherein said cathodehas a smaller work function than that of said anode.
 33. The organicelectroluminescent device as set forth in claim 24, wherein said organiclayer has a thickness in the range of 1 nanometer to 1 micrometer bothinclusive.